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Tom Silverman created Tommy Boy Music in 1981 in his New York City apartment with a $5,000 loan from his parents. The label was an outgrowth of Silverman's Dance Music Report bi-weekly publication, which spanned 14 years, beginning in September 1978.[5]

In 1986, Warner Bros. Records entered into a partnership with Tommy Boy and acquired half of the label, though the label was distributed independently and marketed and promoted its music independently. Warner allowed the label to use independent distribution as it saw fit, with the option to distribute artists through the major-label channel through Warner Bros. Records.[citation needed]

The label had several joint ventures in the mid 1990's including Penalty Recordings,[6] Stepsun,[7] Beyond,[8] and Ignition.[9] The label also had deals with labels such as Timber Records and distribution deals with Outcaste Records[10] and 75 Ark.[11]

In 1997, Tommy Boy launched an imprint label called Upaya to pursue the growing interest in spirituality and spiritual/world music.[12][13] The imprint Tommy Boy Gospel was launched in 1998 under the direction of Max Seigel and Marvie Wright.[14] That same year, the imprints Tommy Boy Black Label,[15] which specialized in underground hip hop music, and Tommy Boy Silver Label,[16] which specialized in dance music, were founded.

In 2002 as part of Warner, Tommy Boy formed Tommy Boy Films, a new TV and film division with Dubtitled Entertainment owner, Michael "Mic" Neumann,[17] while also giving independent distribution to sister imprints that already had label deals with WEA, including American Recordings’ Ill Labels, Mute Records’ NovaMute, and Cold Chillin’s’ Livin’ Large.[18]

In 2002, Tommy Boy became independent again after it ended its joint venture with Warner Bros.[19] Warner acquired the half of the company which it did not own, the master tapes released until that time became property of Warner Music. The then-current Tommy Boy artists were shopped to the various WEA labels, the TV and film divisions were merged with the Tommy Boy music division and the resulting company was redubbed Tommy Boy Entertainment LLC, while the classic trademark remained with Silverman. The label then licensed its trademark to Warner for use on its reissues through Rhino/Atlantic Records.[citation needed]

The Tommy Boy logo was originally designed in 1982 by Steven Miglio and redesigned in 1989 by Eric Haze. The logo was named to Complex's list of The 50 Greatest Rap Logos at number nine.[20]

In the late 1980s, Tommy Boy distributed Carhartt jackets embroidered with its logo for promotional uses, shortly before marketing its own merchandise line to consumers called Tommy Boy Gear.[21][22] The label is also credited as the first to use lanyards as promotional items.[23]